The development of new methodology for the synthesis of pharmacologically important alkaloids constitutes the major focus of this program. The use of oxazoles as azadiene components for the Diels-Alder reaction has been used to prepare substituted pyridine rings, important part structures of numerous alkaloid systems. Present studies have been directed to the regiospecific synthesis of substituted indoles for the preparation of the ergot alkaloids, compounds which are useful in inhibiting prolactin release and for the treatment of Parkinson's disease. The current work relies on the ring opening reactions of aziridines by organometallics to generate the D-ring of these natural products by a "3 atom plus 3 atom" cycloaddition process. The knowledge gained from these studies will be extended to the synthesis of other indole containing alkaloids.